A direct method to obtain α-alkylidene β-oxo amides by the palladium-catalyzed carbonylation of α-chloro ketones in the presence of aromatic imines has been described. The methodology can be applied to a variety of C-aryl imines bearing N-aryl or N-alkyl substituents. The entire process is highly stereoselective and affords the α-alkylidene β-oxo amides only as (Z) isomers. A mechanistic hypothesis involving an acyl-β-lactam intermediate has also been proposed.
Stereoselective synthesis of α-alkylidene β-oxo amides by palladium-catalyzed carbonylation / Perrone, Serena; Salomone, Antonio; Caroli, Antonio; Falcicchio, Aurelia; Citti, Cinzia; Cannazza, Giuseppe; Troisi, Luigino. - In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1434-193X. - STAMPA. - 2014:27(2014), pp. 5932-5938. [10.1002/ejoc.201402666]
Stereoselective synthesis of α-alkylidene β-oxo amides by palladium-catalyzed carbonylation
CANNAZZA, Giuseppe;
2014
Abstract
A direct method to obtain α-alkylidene β-oxo amides by the palladium-catalyzed carbonylation of α-chloro ketones in the presence of aromatic imines has been described. The methodology can be applied to a variety of C-aryl imines bearing N-aryl or N-alkyl substituents. The entire process is highly stereoselective and affords the α-alkylidene β-oxo amides only as (Z) isomers. A mechanistic hypothesis involving an acyl-β-lactam intermediate has also been proposed.File | Dimensione | Formato | |
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